Oxytocin

HCID 439302CAS 50-56-6

기본 정보

표준 SMILES
CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O
InChIKey
XNOPRXBHLZRZKH-DSZYJQQASA-N
분자식
C43H66N12O12S2
평균 분자량
1,007.2 g/mol
단동위원소 질량
1,006.43645755

개요

Oxytocin is a cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour. It has a role as a vasodilator agent and an oxytocic. It is a heterodetic cyclic peptide and a peptide hormone.

이름 및 식별자

우선 이름
Oxytocin
IUPAC
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
영어명
Oxytocin
분자식
C43H66N12O12S2
분자량
1007.19

이름 및 동의어

OXYTOCIN50-56-6PitocinEndopituitrinaSyntocinonOcytocinOrasthinOxitocinaOxytocineOxytocinumOxystinSynthetic oxytocin
이름 더 보기
OTOXTOXTOCINOxytocin powderCYS-TYR-ILE-GLN-ASN-CYS-PRO-LEU-GLY-NH2atonino
Piton S(1-Hemicystine)oxytocinSyntocinonePresoxinSyntocinUteraconDi-sipidinNobitocin S

데이터베이스 식별자

CAS
50-56-6
PubChem CID
439302
DTXSID
DTXSID8048361
ChEMBL
CHEMBL395429
ChEBI
CHEBI:7872
EC Number
200-048-4

물성

구조 계산 물성

XLogP
-2.6
극성 표면적
450 Ų
수소 결합 공여자 수
12
수소 결합 수용자 수
15
회전 가능 결합 수
17
무거운 원자 수
69

실험 및 물리화학적 성질

Color/FormWhite powder
SolubilitySoluble in water, butanol
Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Oxytocics; Pituitary Hormones, Posterior

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Uterotonics

Animal Drugs · 2건

FDA approved animal drugs -> Active ingredient

Pharmaceuticals -> UK Veterinary Medicines Directorate List

DecompositionWhen heated to decomposition it emits toxic fumes of /sulfur oxide/ and /nitric oxide/.
Melting Point192-194 ℃

물리화학적 성질

녹는점
192 · 192-194°C
끓는 점
1533.3 · 1533.3±65.0 °C(Predicted)
밀도
1.1086 · 1.1086 (rough estimate)
굴절률
1.67 · 1.6700 (estimate)
저장 조건
2 · 2-8°C
용해도
물에 매우 잘 녹습니다. 아세트산과 에탄올의 묽은 용액(96%)에 용해됩니다.
화학적 성질 · 1건

Oxytocin is a white to yellowish brown powder, hygroscopic, easily soluble in water. It is a synthetic cyclic nonapeptide having the structure of the hormone produced by the posterior lobe of the pituitary gland that stimulates contraction of the uterus and milk ejection in receptive mammals.

안전 및 규제

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 79.6% (39 of 49) of all reports.

Warning

H302 (10.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationOxytocin: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Oxytocin: Human health tier I assessment
FDA Requirements · 3건

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including oxytocin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Oxytocin is included on this list.

Oxytocin may be used as a uterine contractor to precipitate and accelerate normal parturition and postpartum evacuation of uterine debris. In surgery it may be used postoperatively following cesarean section to facilitate involution and resistance to the large inflow of blood. It will contract smooth muscle cells of the mammary gland for milk letdown if the udder is in proper physiological state. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.

Hazard Classes and CategoriesAcute Tox. 4 (10.2%)
Skin, Eye, and Respiratory IrritationsMay cause irritation. Avoid contact. Avoid inhalation. Remove to fresh air.
Hazardous Reactivities and Incompatibilities · 1건

Oxytocin injection appears to be compatible with most iv infusion fluids but is reported to be physically incompatible with fibrinolysin, norepinephrine bitartrate, prochlorperazine edisylate, and warfarin sodium. Oxytocin injection has also been reported to be incompatible with various other drugs, but the compatibility depends on several factors (eg, the concentration of the drugs, resulting pH, temperature). Specialized references should be consulted for more specific compatibility information.

안전 및 보호

Fire Fighting Procedures · 2건

Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.

As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.

Storage Conditions · 2건

Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.

Oxytocin injection should be stored at temperatures less than 15-25 °C but should not be frozen. Pitocin should be refrigerated at 2-8 °C but may be exposed to temperatures ranging from 15-25 °C for up to 30 days; Pitocin exposed to this latter temperature range for longer periods should be discarded.

Cleanup MethodsWipe up spillage or collect spillage using a high- efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
Disposal Methods · 2건

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Preventive Measures · 3건

This material is assumed to be combustible. As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.

As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.

/Use/ safety goggles or glasses /and/ protect exposed skin.

Personal Protective Equipment (PPE) · 2건

Engineering controls such as exhaust ventilation are recommended.

Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.

독성 정보

Interactions · 3건

Severe hypertension has been reported when oxytocin was given 3-4 hours following prophylactic administration of a vasoconstrictor in conjunction with caudal block anesthesia.

Cyclopropane anesthesia may modify oxytocin's cardiovascular effects, producing less pronounced tachycardia but more severe hypotension than occurs with oxytocin alone; maternal sinus bradycardia with abnormal atrioventricular rhythms has been noted when oxytocin was used concomitantly with cyclopropane anesthesia.

Oxytocin reportedly has delayed induction of thiopental anesthesia by producing venous spasm that caused peripheral pooling of thiopental; however, this interaction has not been conclusively established.

Adverse Effects · 1건

Common adverse reactions associated with oxytocin administration include erythema at the site of injection, intensified contractions, more frequent contractions, nausea, vomiting, stomach pain, and loss of appetite. Serious adverse effects that require monitoring after oxytocin administration include cardiac arrhythmias, seizures, anaphylaxis, confusion, hallucinations, severe blood pressure elevations, and blurred vision.

Milk Concentrations · 1건

Samples of human milk obtained from lactating women in the early postpartum period were assayed for oxytocin concentrations by specific RIA, following extraction procedures with Florisil. Mean oxytocin concentrations in human milk at postpartum day 1 to 5 were 4.5 +/- 1.1, 4.7 +/- 1.1, 4.0 +/- 1.3, 3.2 +/- 0.4, 3.3 +/- 0.6 microunits/mL (+/- SE), respectively. Oxytocin levels in milk were significantly increased by nursing (3.1 +/- 0.6, 5.3 +/- 1.0 microunits/mL, respectively). 3H-oxytocin in human milk was stable even after incubation at 37 degrees C for 2 hours. The dilution curve for milk was parallel to the curve for the standard oxytocin. The chromatographic fraction of immunoreactive oxytocin was identical to that of 3H-oxytocin. 3H-oxytocin was administered to lactating rats. Radioactivity in the neonatal gastric contents and plasma were 12.8% and 4.4% of the counts in the maternal plasma. It was made clear that oxytocin is stable in milk and that oxytocin in maternal blood can be transferred to milk and then to neonates.

Toxicity SummarySigns and Symptoms of Overdose
Natural Pollution SourcesA hormone secreted by the posterior lobe of the pituitary gland. Its chief action is stimulation of the contraction of the smooth muscle of the uterus. It contains eight different amino acids.
Human Toxicity Excerpts · 5건

/HUMAN EXPOSURE STUDIES/ ... Thirty-eight healthy women scheduled for a surgical suction curettage with general anesthesia were enrolled /in this study/ to assess the effect of oxytocin on QT interval. General anesthesia was induced by propofol and maintained by either propofol (n = 18) or sevoflurane (n = 20). Electrocardiographic recordings were obtained before and at 1, 2, 3, and 5 minutes after a 10-U intravenous bolus of oxytocin. Intravenous oxytocin induced a pronounced QTc interval prolongation of 41 +/- 21 ms ( P < 0.0001), which was maximal 1 minute after administration. The QTc interval returned to control values 3 minutes after oxytocin bolus. Oxytocin bolus also induced an increase in heart rate of 19 +/- 10 beats/min and a significant decrease in systolic arterial pressure of 11 +/- 9 mm Hg (both P < 0.0001). The drug used to maintain anesthesia was not an independent factor of QT interval prolongation in ANOVA analysis. Oxytocin intravenous bolus induced a large and transient QTc interval prolongation, suggesting that it may lead to proarrhythmia in circumstances favoring QTc interval increase.

/HUMAN EXPOSURE STUDIES/ ... In humans, oxytocin has been found to enhance trust and the ability to interpret the emotions of others. It has been suggested that oxytocin may enhance facial processing by increasing focus on the eye region of human faces. In a double-blind, randomized, placebo-controlled, between-subject design, /investigators/ tracked the eye movements of 52 healthy male volunteers who were presented with 24 neutral human faces after intranasal administration of 24 IU oxytocin or placebo. Participants given oxytocin showed an increased number of fixations and total gaze time toward the eye region compared with placebo participants. Oxytocin increases gaze specifically toward the eye region of human faces. This may be one mechanism by which oxytocin enhances emotion recognition, interpersonal communication, and social approach behavior in humans. Findings suggest a possible role for oxytocin in the treatment of disorders characterized by eye-gaze avoidance and facial processing deficits.

/HUMAN EXPOSURE STUDIES/ The aim of the work was to compare labor courses, ways of delivery, condition of the newborns in spontaneous and oxytocin-related labors and to analyse the indications for oxytocin administration. 2198 full-term deliveries (pregnant women qualified for elective caesarean section were excluded from the study) at the Provincial Hospital in Przemys'l, Poland. Labors with the adjunctive oxytocin infusion--1102 women. Spontaneous labors (without oxytocin administration)--1096 women. The analysis of the compatibility of measured traits was carried out by the Chi-squared test (Chi2), p < 0.05 was assumed as statistically significant level. Indications for the oxytocin administration: secondary hypokinetic contractions of the uterus (642 labors--58.25%), premature rupture of membranes (176 labors - 15.97 %). Deliveries by caesarean section: 1. study group--187 women (16.97%). 2. control group--97 women (8.85%). Chi2 = 32.192; df = 1; p = 0.0000. Newborns after vaginal labors scored 7 or below according to the Apgar in the first minute after the delivery. 1. study group--35 newborns (8.7%); 2. control group--18 newborns (1.8%) Chi2 = 5.493; df = 1; p = 0.0190. Newborns hospitalized for over 48 hours: 1. study group--346 (31.39%); 2. control group--216 newborns (19.70%). Chi2 = 39.454; df = 1; p = 0.0000. Hypokinetic uterine contractions were the most frequent indication for oxytocin administration during labor. Oxytocin administration increases twice the risk of delivery by the caesarean section. Newborns after vaginal oxytocin-related labours scored 7 or below on the Apgar score in the first minute after the birth when compared to the newborns after spontaneous labor. Oxytocin administration during parturition elongates the time of newborns hospitalization.

/HUMAN EXPOSURE STUDIES/ Oxytocin (OT) effect on ghrelin-stimulated neuropeptide Y (NPY) secretion was evaluated in 12 normal men. Tests: ghrelin (1 ug/kg B.W. as an intravenous bolus); OT (2 mIU/min infusion); ghrelin plus OT; normal saline. Plasma NPY did not change during saline or OT infusions, whereas it showed a significant 29% increase vs baseline at 15 min after ghrelin injection. When OT was present, ghrelin-induced NPY increment was completely abolished. Results show that oxytocin modulates the NPY response to ghrelin, whereas it is unable to produce direct inhibitions of basal circulating NPY levels.

For more Human Toxicity Excerpts (Complete) data for Oxytocin (21 total), please visit the HSDB record page.

규제 정보

FDA Requirements · 3건

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including oxytocin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Oxytocin is included on this list.

Oxytocin may be used as a uterine contractor to precipitate and accelerate normal parturition and postpartum evacuation of uterine debris. In surgery it may be used postoperatively following cesarean section to facilitate involution and resistance to the large inflow of blood. It will contract smooth muscle cells of the mammary gland for milk letdown if the udder is in proper physiological state. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.

안전 데이터

wgk
3
rtecs
RS7534000
ridadr
3249
독성
LD50 oral in rat: > 20520ug/kg
HS 번호
2937190000
risk_code
36/37/38

화학 및 산업

약리 정보

ATC Code · 3건

H - Systemic hormonal preparations, excl. sex hormones and insulins

QH - Systemic hormonal preparations, excl. sex hormones and insulin

H01BB02

Pharmacodynamics · 1건

Oxytocin is a nonapeptide, pleiotropic hormone that exerts important physiological effects. It is most well known to stimulate parturition and lactation, but also has important physiological influences on metabolic and cardiovascular functions, sexual and maternal behaviour, pair bonding, social cognition, and fear conditioning. It is worth noting that oxytocin receptors are not limited to the reproductive system but can be found in many peripheral tissues and in central nervous system structures including the brain stem and amygdala.

Mechanism of Action · 6건

Oxytocin plays a vital role in labour and delivery. The hormone is produced in the hypothalamus and is secreted from the paraventricular nucleus to the posterior pituitary where it is stored. It is then released in pulses during childbirth to induce uterine contractions. The concentration of oxytocin receptors on the myometrium increases significantly during pregnancy and reaches a peak in early labor. Activation of oxytocin receptors on the myometrium triggers a downstream cascade that leads to increased intracellular calcium in uterine myofibrils which strengthens and increases the frequency of uterine contractions. In humans, most hormones are regulated by negative feedback; however, oxytocin is one of the few that is regulated by positive feedback. The head of the fetus pushing on the cervix signals the release of oxytocin from the posterior pituitary of the mother. Oxytocin then travels to the uterus where it stimulates uterine contractions. The elicited uterine contractions will then stimulate the release of increasing amounts of oxytocin. This positive feedback loop will continue until parturition. Since exogenously administered and endogenously secreted oxytocin result in the same effects on the female reproductive system, synthetic oxytocin may be used in specific instances during the antepartum and postpartum period to induce or improve uterine contractions.

The pharmacologic and clinical properties of oxytocin are identical with those of naturally occurring oxytocin principle of the posterior lobe of pituitary. Oxytocin exerts a selective action on the smooth musculature of the uterus, particularly toward the end of pregnancy, during labor, and immediately following delivery. Oxytocin stimulates rhythmic contractions of the uterus, increases the frequency of existing contractions, and raises the tone of the uterine musculature.

Oxytocin indirectly stimulates contraction of uterine smooth muscle by increasing the sodium permeability of uterine myofibrils. High estrogen concentrations lower the threshold for uterine response to oxytocin. Uterine response to oxytocin increases with the duration of pregnancy and is greater in patients who are in labor than those not in labor; only very large doses elicit contractions in early pregnancy. Contractions produced in the term uterus by oxytocin are similar to those occurring during spontaneous labor. In the term uterus, oxytocin increases the amplitude and frequency of uterine contractions which in turn tend to decrease cervical activity producing dilation and effacement of the cervix and to transiently impede uterine blood flow.

Oxytocin contracts myoepithelial cells surrounding the alveoli of the breasts, forcing milk from the alveoli into the larger ducts and thus facilitating milk ejection. The drug possesses no galactopoietic properties.

Oxytocin produces vasodilation of vascular smooth muscle, increasing renal, coronary, and cerebral blood flow. Blood pressure is usually unchanged, but following iv administration of very large doses or undiluted solutions, blood pressure may decrease transiently, and tachycardia and an increase in cardiac output may be reflexly induced. Any initial fall in blood pressure is usually followed by a small but sustained increase in blood pressure. In contrast to vasopressin, oxytocin has minimal antidiuretic effects; however, water intoxication may occur when oxytocin is administered with an excessive volume of electrolyte-free iv fluids and/or at too rapid a rate.

For more Mechanism of Action (Complete) data for Oxytocin (15 total), please visit the HSDB record page.

Biological Half-Life · 2건

The plasma half-life of oxytocin ranges from 1-6 minutes. The half-life is decreased in late pregnancy and during lactation.

Oxytocin has a plasma half-life of about 3 to 5 minutes.

Metabolism/Metabolites · 3건

Oxytocin is rapidly removed from the plasma by the liver and kidney. The enzyme oxytocinase is largely responsible for the metabolism and regulation of oxytocin levels in pregnancy and only a small percentage of the neurohormone is excreted in the urine unchanged. Oxytocinase activity increases throughout pregnancy and peaks in the plasma, placenta and uterus near term. The placenta is a key source of oxytocinase during gestation and produces increasing amounts of the enzyme in response to increasing levels of oxytocin produced by the mother. Oxytocinase activity is also expressed in mammary glands, heart, kidney, and the small intestine. Lower levels of activity can be found in the brain, spleen, liver, skeletal muscle, testes, and colon. The level of oxytocin degradation is negligible in non-pregnant women, men, and cord blood.

Oxytocinase, a circulating enzyme produced early in pregnancy, is also capable of inactivating the polypeptide.

During pregnancy ... "oxytocinase" ... is capable of inactivating oxytocin by cleavage of the 1-cysteine to 2-tyrosine peptide bond.

FDA Pharmacological Classification · 6건

1JQS135EYN

OXYTOCIN

Physiologic Effects [PE] - Increased Uterine Smooth Muscle Contraction or Tone

Established Pharmacologic Class [EPC] - Oxytocic

Chemical Structure [CS] - Oxytocin

Oxytocin is an Oxytocic. The physiologic effect of oxytocin is by means of Increased Uterine Smooth Muscle Contraction or Tone.

용도 및 제조

Uses · 2건

MEDICATION

MEDICATION (Vet)

Methods of ManufacturingObtained from the posterior lobe of the pituitary of healthy hogs or cattle.
Formulations/Preparations · 2건

Oxytocin injection, USP ... contains 10 USP units per mL and may be administered iv or im. All commercial preparations are now synthetic.

... injection, USP

General Manufacturing Information · 2건

Each mL of posterior pituitary injection NF possesses oxytocic activity equivalent to 10 USP posterior pituitary units (permissible range, 8.5-12 units) ... /Posterior pituitary/

The hypotensive response of the chicken is the basis for the USP bioassay for oxytocin.

응용 분야 · 3건

개요Oxytocin is a peptide hormone containing nine amino acids secreted and synthesized by the paraventricular and supraoptic nuclei of the hypothalamus and stored and released by the neurohypophysis. It acts in females by inducing uterine contractions during parturition and stimulating milk ejection by the mammary glands. No actions in males are known. Synthetic derivatives of oxytocin are used to induce labor and for therapeutic abortions. In recent years the safety of oxytocin has been greatly enhanced by the use of continuous maternal and fetal monitoring and by the use of controlled intravenous infusion of the drug.

역사Oxytocin was discovered by Sir Henry Dale in 1909 when he found that an extract from the human posterior pituitary gland contracted the uterus of a pregnant cat. (The hormone is found unchanged in every mammalian species.) Dale named the unknown substance oxytocin, using the Greek words for "quick" and "birth." As early as 1911, physicians began using the pituitary extract to stimulate childbirth contractions. Dale subsequently found that the same extract facilitates the release of mother's milk. In the early 1950s, American biochemist Vincent du Vigneaud found that oxytocin is made up of nine amino acids, and he identified its amino acid sequence. In 1953 du Vigneaud carried out the synthesis of oxytocin, making it the first polypeptide hormone to be synthesized. (Du Vigneaud received the Nobel Prize for Chemistry in 1955 for his breakthrough.)

일반 설명Oxytocin (OXT) is a potent natriuretic hormone encoded by the gene mapped to human chromosome 20p13. It is synthesized along with its carrier protein neurophysin I from its inactive precursor prepro-OXT. OXT gene consists of three exons and two introns, where first exon codes for hormone OXT while other exon codes for neurophysin I.

공급사50 곳

四川多瑞药业有限公司010-52075988 15066320551 · [email protected]
浙江华军药业有限公司0571-17315361885 17315361885 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
추가 설명 · 1건

정의ChEBI: Oxytocin is a cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour. It has a role as an oxytocic and a vasodilator agent. It is a peptide hormone and a heterodetic cyclic peptide.

관련 반응

4건

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